N-(3-iodoprop-2-yn-1-yl)-4-methylbenzenesulfonamide | 55022-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-iodoprop-2-yn-1-yl)-4-methylbenzenesulfonamide
• 英文别名: N-(3-iodoprop-2-ynyl)-4-methylbenzenesulfonamide
• CAS: 55022-47-4
• 化学式: C₁₀H₁₀INO₂S
• 分子量: 335.165
• InChiKey: XKZJCGSPCZVWJD-UHFFFAOYSA-N

物化性质

• 沸点：
  414.4±55.0 °C(Predicted)
• 密度：
  1.750±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-iodoprop-2-yn-1-yl)-4-methylbenzenesulfonamide 在 copper(l) iodide 、 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 、 potassium acetate 、 caesium carbonate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 1-benzyl-6-phenyl-5-tosyl-4,5-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridine
  参考文献：
  名称：

  一种新的多组分多催化剂反应（MC）2 R：化学选择性环加成反应和潜在的催化剂活化，用于合成完全取代的1,2,3-三唑

  摘要：

  的多组分multicatalyst反应（MC）2 R代表构建完全取代的1,2,3-三唑报道。化学选择性和潜在催化在一系列多催化反应中的应用赋予了许多不希望有的过程控制权，在这些过程中所有试剂共存于同一反应容器中。化学选择性铜催化的叠氮化物炔烃环加成的顺序，然后钯/铜催化的Sonogashira交叉偶联，可以选择性地从1,2-3-三唑以高收率和高收率提供广泛的应用范围。

  DOI：

  10.1021/acs.orglett.6b00975
• 作为产物：
  描述：

  对甲苯磺酰氯 在 碘 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 N-(3-iodoprop-2-yn-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis of 1,2,3-triazole-fused heterocycles viaPd-catalyzed cyclization of 5-iodotriazoles

  摘要：

  描述了一种方便的方法来合成含有融合1,2,3-三唑的多环框架。该合成包括Cu催化的环加成反应和一种分子内Pd催化的直接芳基化或Heck反应，最终产物的收率良好至优异。

  DOI：

  10.1039/c1cc16110e

文献信息

• A systematic study on the Cadiot–Chodkiewicz cross coupling reaction for the selective and efficient synthesis of hetero-diynes
  作者：Bhavani Shankar Chinta、Beeraiah Baire

  DOI：10.1039/c6ra07308e

  日期：——

  99% selectivity for cross coupling. Excellent yields (upto 94%). Low basic reaction medium, high functional group tolerance. Use of green solvent water.

  99%的交叉偶联选择性。产率优异（高达94%）。反应介质碱性低，官能团耐受性高。使用绿色溶剂水。
• Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling
  作者：Yury N. Kotovshchikov、Stepan S. Tatevosyan、Gennadij V. Latyshev、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1055/a-1623-2333

  日期：2022.1

  Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I

  一种方便的方法来组装 1,2,3-三唑融合的 4H-3,1-苯并恶嗪。多种醇系 5-碘三唑，可通过 Cu 催化 (3+2)-环加成的改进方案轻松获得，被用作目标稠合杂环的前体。分子内 C-O 偶联在无碱介导的过渡金属条件下有效进行，环化产物的产率高达 96%。通过在 100 °C 的乙腈中使用 Na2CO3 来抑制 C-I 键的竞争性还原裂解。这种实用且具有成本效益的程序具有广泛的底物范围和宝贵的官能团耐受性。
• Structure optimization and bioactivity evaluation of ThDP analogs targeting cyanobacterial pyruvate dehydrogenase E1
  作者：Jiangtao Feng、Haifeng He、Yuan Zhou、Meng Cai、Hao Peng、Honglin Liu、Lei Liu、Lingling Feng、Hongwu He

  DOI：10.1016/j.bmc.2019.115159

  日期：2019.12

  Harmful cyanobacteria bloom (HCB) has occurred frequently in recent years and it is urgent to develop novel algicides to deal with this problem. In this paper, a series of novel thiamin diphosphate (ThDP) analogs 5a-5g were designed and synthesized targeting cyanobacterial pyruvate dehydrogenase complex E1 (Cy-PDHc E1). Our results showed that compounds 5a-5g have higher inhibitory activities against Cy-PDHc E1 (IC50 9.56-3.48 mu M) and higher inhibitory activities against two model cyanobacteria strains Synechocystis sp PCC6803 (EC50 2.03-1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 1.86-0.95 mu M). Especially, compound 5b displayed highest inhibitory activities (IC50 = 3.48 mu M) against Cy-PDHc E1 and powerful inhibitory activities against cyanobacteria Synechocystis sp PCC6803 (EC50 = 1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 = 1.04 mu M). Moreover, the inhibitory activities of compound 5b were even higher than those of copper sulfate (EC50 = 2.02 and 1.71 mu M separately) which has been widely used as algicide against cyanobacteria PCC6803 and FACHB905. The more important was that compound 5b display much higher inhibitory selectivity between Cy-PDHc E1 (Inhibitory rate 97.4%) and porcine PDHc E1 (Inhibitory rate 11.8%) under the same concentration (100 mu M). The inhibition kinetic experiment and molecular docking research showed that compound 5b can inhibit Cy-PDHc E1 by occupying the ThDP-binding pocket and then blocking Cy-PDHc E1 bound to ThDP as competitive inhibitor. The imagines of SEM and TEM showed that cellular microstructures were heavily destroyed under compound 5b stress. Our results demonstrated compound 5b could be taken as a potential lead compound targeting Cy-PDHc E1 to obtain environment-friendly algicide for harmful cyanobacterial blooms control.